Total Synthesis of Isorosthin L and Isoadenolin I

被引：13

作者：

Ao, Junli ^{[1
,2
]}

Sun, Chao ^{[2
]}

Chen, Bolin ^{[1
]}

Yu, Na ^{[2
]}

Liang, Guangxin ^{[2
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 10期

基金：

中国国家自然科学基金;

关键词：

Aldol reaction; ent-Kaurane diterpenoids; Natural products; Radical cyclization; Total synthesis; ENT-KAURANE DITERPENOIDS; UNIFIED STRATEGY; OXIDATION; ALCOHOLS; OLEFINS; ACID;

D O I：

10.1002/anie.202114489

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total syntheses of two Isodon diterpenes, isorosthin L and isoadenolin I, are reported. The synthetic strategy features a quick assembly of two simple building blocks through a diastereoselective intermolecular aldol reaction and a subsequent radical cyclization for efficient construction of a rather complex advanced intermediate bearing a quaternary stereocenter present in all Isodon diterpenes. Oxidative cleavage of the C-C bond in the cyclopentane enabled the conversion to a lactone moiety which is desired for the construction of the molecular skeleton through reductive coupling with an aldehyde carbonyl group.

引用

页数：5

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